Abstract
Chemists have long been intrigued by the molecular basis of isomerism. Indeed, much of the powerful paradigm of structure based upon the molecular graph was first invented to explain isomerism, including the classifications used in modern stereochemistry. Thus, constitutional isomers describe pairs of isomeric molecular structures possessing non-homeomorphic molecular graphs, while the classical stereoisomers (enantiomers and diastereomers) possess molecular graphs which are homeomorphic and also homeotopic (interconvertable by continuous deformation in 3-space). This means that classical stereoisomerism is derived from the Euclidean properties of molecular graphs, being a manifestation of some kind of molecular rigidity.
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Walba, D.M. (1991). A Topological Hierarchy of Molecular Chirality and other Tidbits in Topological Stereochemistry. In: Mezey, P.G. (eds) New Developments in Molecular Chirality. Understanding Chemical Reactivity, vol 5. Springer, Dordrecht. https://doi.org/10.1007/978-94-011-3698-3_4
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